


Long Night

by TongueTiedMisfit



Category: Supernatural
Genre: Condoms, Destiel - Freeform, Father-Son Relationship, Fluff, Idiots in Love, Judence, Other, Phone Calls, Sex Talk, Supportive Dean Winchester, Uncomfortable Conversations, fluffy crap, thank you snailhair for my boys
Language: English
Status: Completed
Published: 2019-11-01
Updated: 2019-11-01
Packaged: 2021-01-16 14:17:48
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,608
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21272576
Author URL: https://archiveofourown.org/users/TongueTiedMisfit/pseuds/TongueTiedMisfit
Summary: The conversation needs to be had, but that doesn’t make Jude feel any better about it.





	Long Night

**Author's Note:**

  * For [Snailhair](https://archiveofourown.org/users/Snailhair/gifts).
  * Inspired by [Faith](https://archiveofourown.org/works/13621323) by [Snailhair](https://archiveofourown.org/users/Snailhair/pseuds/Snailhair). 

> I can’t believe I’m actually posting this I’m excited! A little background: this is set a few weeks/months after the events in Snailhairs “Faith” (if you haven’t read her Purpose series, this probably won’t make much sense, but you should go and read that because it’s awesome and I’m obsessed with it) Dean and Jude are headed up to Bobby’s to go on a hunt together, but Jude and Clarence have other plans ;) sorry about the summary I am not good at those. Also: Jude, Clarence, Jessica, and Oliver all belong to Snailhair

Night Superman. I can’t wait to see you-C

A bashful grin bloomed on Jude’s face when he read his boyfriends sweet message. Clarence could be such a sap sometimes. The nephilim sent his boyfriend one last text before plugging his phone up to the charger: 

Goodnight sweetheart. I love you. -J

Okay, maybe they were both a little sappy. A little bubble of excitement burst inside Jude’s chest and he giggled into his pillow. He was going to see Clarence this weekend! His boyfriend! He picked up his phone once again to take a look at his lock screen picture: Clarence sitting on his bed playing guitar, his long golden hair pulled up in a bun, and three cookies stuffed in his mouth as he made a goofy face at the camera. 

Another laugh burst from Jude as he looked at the candid picture of his beloved goofball. He’d taken the picture last time they got to hang out together a few weeks ago. It had been the first time since the Darkness fiasco that he felt he’d totally been able to relax, like nothing bad had ever happened. Of course, some good things had come out of their experience with the Darkness: Adam was well again, they’d gotten to see grandpa Chuck again, the Winchester’s had saved the world yet again…. 

He and Clarence had had sex for the first time… 

The two boys hadn’t really talked about the experience since it had happened a few weeks before. The act had been a huge step for them and they were both a little nervous about touching on the subject again. Until tonight, that is. 

::::::::

Jude called Clare like he usually did in the evening, so the boys could tell each other about their days and gush about how much they missed each other. And, at least once a night Jessie would poke her head into Jude’s bedroom to make gagging faces when she heard their conversations getting too “lovey-dovey”. 

“Get out!” Jude mouthed at his cousin so he didn’t interrupt what Clare was saying on the other side. 

A trademark Trickster grin broke out on Jessica’s face, “I’m sorry, I can’t read your lips. I can’t see through all of the awful love fumes in the air!” 

Jude made a rude hand gesture at her that papa definitely wouldn’t approve of. The blonde nephilim scoffed at her cousin and turned on her heel and out of the room, clearly offended. Whatever, Jude thought, she’ll get over it. It wasn’t like her and Ollie were any less romantic with each other. At least Jude and Clare didn’t have cheesy pet names for each other. 

“Babe?” 

Jude pulled the phone back to his ear, “Sorry, Jess is being annoying.” 

Clarence chuckled on the other line (Jude’s favorite sound) “As usual…. Anyway, I was asking what you wanna do this weekend.” 

The half angel thought for a moment before answering, “Well, I really want dad and Bobby to let us help with this case, but they’re not gonna let us help with fun monster-killing unless we help with the boring monster-researching.” He rolled his eyes, “And I’d really rather spend the down time with you.” 

“You’ll be with me.” Clare chided. 

Jude sighed and smiled, “You know what I mean numb-nuts. I want some alone time with my super hot demon boyfriend.” 

“Well we’ll just blow off the hunt. There’ll be another one next week, and the week after that. Plus they’d rather us stay out of harm’s way, so they’ll probably let us do whatever we want.” 

“Huh,” Jude had to admit, Clare had a point, “Whatever we want?” 

There was a pause on the other line and Jude mentally kicked himself. He usually didn’t let suggestive stuff slip out around Clarence, but tonight he was tired and it just kinda came out… 

Surprisingly, the half-demon went along with it, “Yeah Jaybird, whatever we want.” 

Jude bit his lip as he began getting a tingly feeling in the pit of his stomach. Okay. They were both definitely talking about the same thing now. Jude gently put his phone on his pillow and dashed across his bedroom to shut the door. He really didn’t want anyone else in the bunker overhearing this conversation. 

Over an hour later, the two teens were bidding one another goodnight via text after a long, personal conversation. 

Jude’s excitement died down a bit as his thoughts drifted over to the more serious side of things. He and Clarence hadn’t exactly, specifically said that they’d be ‘getting busy’ this weekend; they were just sort of putting it out there as something they could be doing. Something that (based off of the tone of their conversation) they probably would most likely be doing if they got more than five minutes alone together. Which meant they would be needing ‘protection’.... 

A different kind of tingly feeling grew in Jude’s stomach. Nervous-tingly. Last time, dad had given him the condom they’d used, and something told Jude that Clarence probably didn’t have any. Both boys were currently broke, and while Jude knew that Bobby and Clare were close, he wasn’t sure if they were ‘hey man can you buy me some condoms’ close. Which meant… 

Jude was going to have to ask his dad for more. Which meant he’d have to tell him that he and Clarence had had sex. 

Jude sat up and prepared to give himself a pep talk. The only person who knew about what he and the half-demon had done was Jessica. Although she was his best friend, he didn’t even want her to know. Jessie finding out had been a total accident. And an embarrassing one. Unfortunately, she would no longer be the only one that knew. He had to tell dad sooner or later. The teenager sighed and stood up. He supposed it would be better to have an awkward conversation with his dad now than not be able to have any ‘fun’ with his boyfriend this weekend. 

You need a plan, though, he thought, If I seem responsible and like I know what I’m talking about maybe he won’t be mad. Surely dad wouldn’t be mad, would he? He was the one that gave Jude the condom in the first place. He’d basically given them permission to do it, right? He would probably do it again. 

Jude looked at his wary reflection in the mirror as he planned out what to say to his father. This was going to be a long night… 

\-------

Dean’s eyes ached as he stared at the bright laptop screen. The clock was going on midnight and it was one of those nights where sleep didn’t find the hunter easily. His angelic husband was off somewhere in the bunker, probably doing late night laundry or piddling around in the library with Sam. Meanwhile, the eldest Winchester was sitting up in bed and sipping a lukewarm beer as he scrolled through crime blogs. Though he was a bit bored out of his mind, Dean has found he appreciated the silence sometimes. Living with five other people and a dog could get on a person’s nerves. Even he and Cas needed some moments to themselves once in a while. Tonight, however, was not really one of those times. Dean really wanted Castiel to come back to bed and cuddle him to sleep, but the hunter didn’t want to force his husband away from whatever he was doing. 

His loneliness didn’t last much longer though. The bedroom door creaked open, breaking the deafening silence of the room. Dean looked up from his computer, just in time to lock eyes with his teenage son peeking into the room. 

The hunter smiled at his son, “Hey there, lil’ man.” Jude smiled in return and stepped into the room. Dean pulled back the covers next to him and gestured for his son to sit, “Why you up so late? Bad dream?” Jude had suffered a few sleepless nights since the Winchester’s latest apocalypse and had spent a handful of those nights squished between his fathers, where they made sure no nightmares plagued their son.

The teen shook his head, seeming hesitant to sit down next to his father, “Um, where’s papa?” 

Dean shrugged, “I think he’s in the library. Why?” 

Jude took a breath before he spoke, fingers picking at the hem of his worn out Pink Floyd t-shirt. That nervous habit had been picked up from Castiel. Dean smiled inwardly at the little similarity between his son and husband, but was more concerned with why Jude seemed so nervous. 

“Well,” Jude started, “I kinda wanted to talk to you about something… alone.” 

Hmm. What was Jude so nervous about that he didn’t want Cas to hear? Was he in some kind of trouble? The hunter patted the space next to him again. This time, Jude sat down. Dean closed the laptop and sat it on his nightstand, ready to give his son his full attention, “So what’s up? Something wrong?” 

“No!” Jude answered quickly. Dean blinked at the tiny outburst. 

“Sorry,” Jude sighed sheepishly. 

“No, it’s okay,” Dean said, “What’s on your mind?” 

Jude took a deep breath and looked at his lap as he fiddled with the edge of the comforter. Why was he so nervous? The elder hunters mind was going to the worst-case scenarios as his son took another breath and looked up, “Well…. I… um…. I-I…. uh…” 

“Spit it out, Jude.” 

“I need condoms.” The teenager blurted. 

Oh. 

Dean didn’t react for a moment. Oh. Okay. Jude needed a condom. Which meant… Okay. He could be cool about this. He’d given Jude one already, he could do it again. It was just weird hearing that sort of request come out of his little boys mouth. 

“Oh,” he finally answered, “Oh, okay. Um, yeah, okay. So...” Talk, Dean, you need to talk about this, “Sooo, I’m assuming this means you, uh, used the one I gave you?” 

Jude nodded. 

“Okay. Okay, so… so that means you and Clarence….” Dean drifted off. 

Jude pulled his knees up to his chest, hiding part of his face as he slowly nodded, “We had sex.” The statement was almost too quiet for Dean to hear. 

He suddenly felt nauseous. Deep breaths, Dean. The hunter wasn’t sure why he was having such a hard time grasping what he was hearing. Of course Jude and Clare had sex, Dean had pretty much given them an invitation. What teenage boys wouldn’t bone at the first chance they got to? God knows Dean had. Oh no, had he set a bad example for his son? He’d just wanted him to be safe with whatever he’d been doing. What if he hadn’t been doing anything at all and Dean had made him feel pressured to stuff? What if Dean had gone about this all the wrong way? What if- 

“Are you mad at me?” 

Deans head whipped up to meet his sons timid gaze. Mad at him? What? Why would Dean be angry? 

“What- no, course not!” Dean exclaimed, his face softening, “What makes you think I’m mad?” 

His son shrugged, “I don’t know, you just got quiet for a long time, I thought…” he trailed off and shrugged again. 

Dean took a deep breath, trying to choose his words carefully. This conversation had gotten awkward very fast, and Dean didn’t want that to be the case here. He wanted Jude to be able to talk to him about anything without feeling uncomfortable. “Bud, listen. I’m not mad or- or disappointed or anything. I j-just…” the oldest Winchester paused for a moment to look at his son. He smiled softly, “Actually… I’m proud of you.” 

Jude sat up straight, brows furrowed in confusion. “You’re proud of me for having sex?” 

Dean chuckled. Jesus Christ, that kid was Castiel made over. “No, bub, I’m just realizing how grown up you are- again. You’re being responsible and doing the adult thing by coming to me to talk about this stuff.” 

“Oh,” Jude smiled, “Uh, thanks.” 

“Ain’t no thing, lil’ man,” Dean patted his son on the shoulder, “So…if you don’t mind me asking, when did you and Clare, uh... ya know…” 

Jude stretched out a bit more, shoulders slumping against the headboard. The teen hesitated a moment before answering. 

“Um… during all of the Darkness… uh, stuff.” 

“Really?! During the mini-apocalypse? What, you see an opportunity since your parents were trapped in Purgatory?”

Jude’s eyes widened in shock as he sort of shook his head, “N-no, it… it just kinda happened!” 

Dean laughed softly, “I’m just messing with ya, bud. It’s usually best if things just kinda happened, you don’t wanna force anything like that, ya know?” Jude nodded, “But, it’s also important to be prepared beforehand, which is why I gave you the condom.” 

Jude nodded again, “You, uh- you wouldn’t happen to have any more of those around here, would you?” 

“Yeah, there’s a box under the bed.” 

Jude started to get up, but paused for a second and sat back down, looking upset again. Oh no, what now? Was a box too many? Did Jude remember how they worked? Surely he did. Jude cleared his throat before speaking again, “Could- well… are you gonna tell papa about this?” 

“Well, I was,” Dean spoke after a moment of hesitation, “Why? Do you not want me to?”

Jude sighed and crossed his legs, looking down at his hands in his lap. Why didn’t Jude want Cas to know? Was he embarrassed? Ashamed? He told Castiel everything!

“I don’t know,” He spoke softly after a moment, “I don’t want- I mean, I feel like he’s just gonna get upset about it.” 

Well, his son had a point there. Cas didn’t care for the fact that the two boys even kissed, if he knew they had... yes, Dean had to admit, Jude had a point, “Well, yeah, papa’s not exactly gonna be ‘gung-ho’ on this whole thing, at least not at first. But, if you talk to him-” 

“I can’t tell him!” Jude’s face began to turn red with embarrassment. 

“Jude, he’s not gonna be mad at you. How come you don’t want to tell him?” Dean knew the question sounded stupid as soon as it left his mouth. Obviously, no kid wanted to tell their parents about their sex life, but if that kid was still a minor living with their parents (who had to come to them for condoms in the first place), then he thought yes, Cas probably needed to know what was going on. 

Jude’s troubled gaze met his fathers as he spoke, “I just… I dunno, I don’t want him to think of me differently, or start treating me different. He gets so upset about me growing up…. I know you don’t like it either, but you’re cool about this kind of stuff.” He looked back down at his lap, “I- I’ll tell him… sometime. I’m just not ready for him to know yet.” 

Sighing softly, Dean tossed an arm around his son’s shoulders and pulled him close, “That’s fine, kiddo. It’s your life, you can tell him whenever you’re ready.” He kissed the top of his boy’s head, “So, anything else you wanna talk about?” Jude rested his head on his father’s chest as he thought. If he had anymore questions, now was the time to ask. 

“How old were you your first time?” 

Dean sighed again, trying to think of a way to tell that story where he didn’t come off like an irresponsible little punk. 

This was gonna be a long night after all.

**Author's Note:**

> Sorry if the ending was kind of abrupt and weird, I have always had trouble writing conclusions (which is why this took me so long to post lol) I tried really hard to keep the characters as close to Snailhairs characterization as possible, I hope I did a good job. Poor Jude gets so uncomfortable! I tried to throw some of Castiel’s mannerisms in there, like I think I remember him fiddling with his shirt in Purpose when he was nervous, and that time (I think season 10) when he called Sam but Dean picked up, and dean asked if anything was wrong and Cas yelled “NO” that will always be one of my favorite moments lol  
Anyway, Snailhair, I hope you enjoyed this fluffy little oneshot! (I’m a sucker for awkward fluffy sex convos. Is that weird lol?) Let me know what you think! I have another one set after this (with some Judence smut ;) because I suck lol) BUT as usual I cannot write an ending to save my life. I may just post it how it is and ask you all for pointers on how to conclude it. Once again, Jude, Clare, Jessie, and Oliver are not my character and belong to Snailhair. Thank you for reading!!


End file.
